5,6-bis[(4-fluorophenyl)amino]-2,3-dihydro-1H-isoindole-1,3-dione

• ChemBase ID: 155644
• Molecular Formular: C20H13F2N3O2
• Molecular Mass: 365.3329264
• Monoisotopic Mass: 365.09758311
• SMILES: c1cc(ccc1Nc1cc2c(cc1Nc1ccc(cc1)F)C(=O)NC2=O)F
• Canonical SMILES: Fc1ccc(cc1)Nc1cc2C(=O)NC(=O)c2cc1Nc1ccc(cc1)F
• InChI: InChI=1S/C20H13F2N3O2/c21-11-1-5-13(6-2-11)23-17-9-15-16(20(27)25-19(15)26)10-18(17)24-14-7-3-12(22)4-8-14/h1-10,23-24H,(H,25,26,27)
• InChIKey: RONQPWQYDRPRGG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,6-bis[(4-fluorophenyl)amino]-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: 5,6-bis[(4-fluorophenyl)amino]-2H-isoindole-1,3-dione
• Synonyms: 5,6-Bis[(4-fluorophenyl)amino]-2H-isoindole-1,3-dione; DAPH 2; CGP-53353

Database IDs

• CAS Number: 145915-60-2
• MDL Number: MFCD00938569
• PubChem SID: 24892990; 162249782
• PubChem CID: 6711154

CALCULATED PROPERTIES

• Acid pKa: 8.730974
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.858426
• LogD (pH = 7.4): 3.8391004
• Log P: 3.8586786
• Molar Refractivity: 96.72 cm^3
• Polarizability: 34.986958 Å^3
• Polar Surface Area: 70.23 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: orange solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... EGFR(1956)

Product Information

• Empirical Formula (Hill Notation): C20H13F2N3O2

DETAILS

Sigma Aldrich - C7866

Biochem/physiol Actions
Selective PKCβII inhibitor. IC50 - 410 nM for PKCβII vs 3.8 μM for PKCβI. Inhibits nPKCs and aPKCs only above 22 μM and other kinases such as protein kinase A, casein kinase I and II, c-src kinase, c-lyn kinase, c-fgr kinase, and v-abl kinase at an IC50 of greater than 50 μM.